Synthesis of Indoles Using Cyclization of Imidoyl Radicals

W. Russell Bowman; Anthony J. Fletcher; Peter J. Lovell; Jan M. Pedersen

doi:10.1055/s-2004-830868

LETTER

Synthesis of Indoles Using Cyclization of Imidoyl Radicals

W. Russell Bowman*^a, Anthony J. Fletcher^a, Peter J. Lovell^b, Jan M. Pedersen^a
^a Department of Chemistry, Loughborough University, Loughborough, Leics. LE11 3TU, UK
Fax: +44(1509)223925; e-Mail: w.r.bowman@lboro.ac.uk;
^b Psychiatry Medicinal Chemistry III, GlaxoSmithKline, New Frontiers Science Park North, Harlow, Essex CM19 5AW, UK

Abstract

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Abstract

Imidoyl radicals, generated from imidoyl phenylselanide precursors, have been used for the synthesis of 2,3-disubstituted indoles. A facile high yielding synthesis of imidoyl phenylselanides has been developed. The potential for neophyl rearrangement of 5-exo radical intermediates to 6-endo radical intermediates is discussed.

Key words

radicals - radical reactions - indoles - cyclizations - rearrangements

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References

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